Rhea - reaction knowledgebase

Enzymes

UniProtKB ^help_outline	852 proteins
Enzyme class ^help_outline	EC 2.4.1.148 acetylgalactosaminyl-O-glycosyl-glycoprotein beta-1,6-N-acetylglucosaminyltransferase

Reaction participants Show >> << Hide

Name^help_outline 3-O-[N-acetyl-β-D-glucosaminyl-(1→3)-N-acetyl-α-D-galactosaminyl]-L-seryl-[protein] Identifier RHEA-COMP:11691 Reactive part ^help_outline
- Name ^help_outline N-acetyl-β-D-glucosaminyl-(1→3)-N-acetyl-α-D-galactosaminyl-L-serine residue Identifier CHEBI:87079 Charge 0 Formula C19H31N3O12 SMILES^help_outline CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H](O)[C@@H](CO)O[C@H](OC[C@H](N-*)C(-*)=O)[C@@H]1NC(C)=O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 2 reaction(s) Find proteins in UniProtKB for this molecule
Name ^help_outline UDP-N-acetyl-α-D-glucosamine Identifier CHEBI:57705 (Beilstein: 4286654) ^help_outline Charge -2 Formula C17H25N3O17P2 InChIKey^help_outline LFTYTUAZOPRMMI-CFRASDGPSA-L SMILES^help_outline CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1ccc(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 88 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name^help_outline 3-O-[N-acetyl-β-D-glucosaminyl-(1→3)-[N-acetyl-β-D-glucosaminyl-(1→6)]-N-acetyl-α-D-galactosaminyl]-L-seryl-[protein] Identifier RHEA-COMP:14412 Reactive part ^help_outline
- Name ^help_outline O³-[N-acetyl-β-D-glucosaminyl-(1→3)-[N-acetyl-β-D-glucosaminyl-(1→6)]-N-acetyl-α-D-galactosaminyl]-L-serine residue Identifier CHEBI:139581 Charge 0 Formula C27H44N4O17 SMILES^help_outline [C@H]1([C@@H]([C@H]([C@H]([C@H](O1)CO[C@]2([C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)NC(=O)C)[H])O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)NC(=O)C)NC(=O)C)OC[C@@H](C(=O)*)N* 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 1 reaction(s) Find proteins in UniProtKB for this molecule
Name ^help_outline UDP Identifier CHEBI:58223 Charge -3 Formula C9H11N2O12P2 InChIKey^help_outline XCCTYIAWTASOJW-XVFCMESISA-K SMILES^help_outline O[C@@H]1[C@@H](COP([O-])(=O)OP([O-])([O-])=O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 611 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline H⁺ Identifier CHEBI:15378 Charge 1 Formula H InChIKey^help_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILES^help_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,717 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:56188	RHEA:56189	RHEA:56190	RHEA:56191
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	852 proteins
EC numbers ^help_outline	2.4.1.148
KEGG ^help_outline				R05915
MetaCyc ^help_outline		2.4.1.148-RXN

Publications

Mucin synthesis. UDP-GlcNAc:GalNAc-R beta 3-N-acetylglucosaminyltransferase and UDP-GlcNAc:GlcNAc beta 1-3GalNAc-R (GlcNAc to GalNAc) beta 6-N-acetylglucosaminyltransferase from pig and rat colon mucosa.

Brockhausen I., Matta K.L., Orr J., Schachter H.

Pig and rat colon mucosal membrane preparations catalyze the in vitro transfer of N-acetyl-D-glucosamine (GlcNAc) from UDP-GlcNAc to GalNAc-ovine submaxillary mucin to form GlcNAc beta 1-3GalNAc-mucin. Rat colon also catalyzes the in vitro transfer of GlcNAc from UDP-GlcNAc to GlcNAc beta 1-3GalNA ... >> More

Pig and rat colon mucosal membrane preparations catalyze the in vitro transfer of N-acetyl-D-glucosamine (GlcNAc) from UDP-GlcNAc to GalNAc-ovine submaxillary mucin to form GlcNAc beta 1-3GalNAc-mucin. Rat colon also catalyzes the in vitro transfer of GlcNAc from UDP-GlcNAc to GlcNAc beta 1-3GalNAc-mucin to form GlcNAc beta 1-3(GlcNAc beta 1-6) GalNAc-mucin. This is the first demonstration of in vitro synthesis of the GlcNAc beta 1-3GalNAc disaccharide and of the GlcNAc beta 1-3-(GlcNAc beta 1-6)GalNAc trisaccharide, two of the four major core types found in mammalian glycoproteins of the mucin type, i.e., those containing oligosaccharides with GalNAc-alpha-serine (threonine) linkages. The activity catalyzing synthesis of the disaccharide has been named UDP-GlcNAc:GalNAc-R beta 3-N-acetylglucosaminyltransferase (mucin core 3 beta 3-GlcNAc-transferase), while the activity responsible for synthesizing the trisaccharide has been named UDP-GlcNAc:GlcNAc beta 1-3GalNAc-R (GlcNAc to GalNAc) beta 6-N-acetylglucosaminyltransferase (mucin core 4 beta 6-GlcNAc-transferase). The beta 3-GlcNAc-transferase from pig colon is activated by Triton X-100, has an absolute requirement for Mn2+, and transfers GlcNAc to GalNAc-alpha-phenyl, GalNAc-alpha-benzyl, and GalNAc-ovine submaxillary mucin with apparent Km values of 5, 2, and 3 mM and Vmax values of 59, 62, and 37 nmol h-1 (mg of protein)-1, respectively.(ABSTRACT TRUNCATED AT 250 WORDS) << Less

Biochemistry 24:1866-1874(1985) [PubMed] [EuropePMC]

This publication is cited by 3 other entries.
The separation by liquid chromatography (under elevated pressure) of phenyl, benzyl, and O-nitrophenyl glycosides of oligosaccharides. Analysis of substrates and products for four N-acetyl-D-glucosaminyl-transferases involved in mucin synthesis.

Brockhausen I., Rachaman E.S., Matta K.L., Schachter H.

Liquid chromatography under elevated pressure (h.p.l.c.) has been applied to the separation of the phenyl, benzyl, and O-nitrophenyl glycosides of 2-acetamido-2-deoxy-D-galactopyranose and of various mucin-type, di-, tri-, and tetra-saccharides. The separations were carried out with a Whatman Part ... >> More

Liquid chromatography under elevated pressure (h.p.l.c.) has been applied to the separation of the phenyl, benzyl, and O-nitrophenyl glycosides of 2-acetamido-2-deoxy-D-galactopyranose and of various mucin-type, di-, tri-, and tetra-saccharides. The separations were carried out with a Whatman Partisil PXS 5/25 PAC column and various proportions of acetonitrile and water in the mobile phase. These methods were subsequently used to separate the substrates and products of the following N-acetylglucosaminyltransferase reactions: UDP-GlcNAc + beta-Gal-(1 leads to 3)-GalNAc-R leads to beta-Gal-(1 leads to 3)-[beta-GlcNAc-(1 leads to 6)]-GalNAc-R + UDP (1); UDP-GlcNAc + beta-Gal-(1 leads to 3)-[beta-GlcNAc-(1 leads to 6)]-GalNAc-R leads to beta-GlcNAc-(1 leads to 3)-beta-Gal-(1 leads to 3)-[beta-GlcNAc-(1 leads to 6)]-GalNAc-R + UDP (2); UDP-GlcNAc + GalNAc-R' leads to beta-GlcNAc-(1 leads to 3)-GalNAc-R' + UDP (3); and UDP-GlcNAc + beta-GlcNAc-(1 leads to 3)-GalNAc-R' leads to beta-GlcNAc-(1 leads to 6)-[beta-GlcNAc-(1 leads to 3)]-GalNAc-R' + UDP (4), where R is = benzyl or o-nitrophenyl, and R' = benzyl or phenyl alpha-D-glycoside. Reaction 1 is catalyzed by a transferase in canine submaxillary glands and porcine gastric mucosa, and reaction 2 by an enzyme in porcine gastric mucosa. Enzyme activities catalyzing reactions 3 and 4 have recently been demonstrated in rat colonic mucosa. Liquid chromatography can be used at the preparative level for the purification and identification of the transferase products, and at the analytical level in the assay of glycosyltransferases. << Less

Carbohydr Res 120:3-16(1983) [PubMed] [EuropePMC]

This publication is cited by 8 other entries.

RHEA:56188 3-O-[N-acetyl-beta-D-glucosaminyl-(1->3)-N-acetyl-alpha-D-galactosaminyl]-L-seryl-[protein] + UDP-N-acetyl-alpha-D-glucosamine = 3-O-[N-acetyl-beta-D-glucosaminyl-(1->3)-[N-acetyl-beta-D-glucosaminyl-(1->6)]-N-acetyl-alpha-D-galactosaminyl]-L-seryl-[protein] + UDP + H(+)

Enzymes

Reaction participants Show >> << Hide

Cross-references

Publications

Mucin synthesis. UDP-GlcNAc:GalNAc-R beta 3-N-acetylglucosaminyltransferase and UDP-GlcNAc:GlcNAc beta 1-3GalNAc-R (GlcNAc to GalNAc) beta 6-N-acetylglucosaminyltransferase from pig and rat colon mucosa.

The separation by liquid chromatography (under elevated pressure) of phenyl, benzyl, and O-nitrophenyl glycosides of oligosaccharides. Analysis of substrates and products for four N-acetyl-D-glucosaminyl-transferases involved in mucin synthesis.